NP-MRD: Showing NP-Card for paraphaeolactone C2 (NP0333604)

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Record Information

Version

2.0

Created at

2024-07-12 04:47:31 UTC

Updated at

2024-09-16 10:46:35 UTC

NP-MRD ID

NP0333604

Natural Product DOI

https://doi.org/10.57994/3083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paraphaeolactone C2

Description

Paraphaeolactone C2 belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Based on a literature review very few articles have been published on paraphaeolactone C2.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03262307212D          

 25 29  0  0  1  0            999 V2000
    2.1427    1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899    0.9995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6649    0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915   -0.6748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1620   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0742   -0.2747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844   -0.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5089    0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0325    1.3390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765   -0.8434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1245    0.7311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9578    1.5391    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.5866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8995    1.3416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1621    0.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5465    0.7557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0076    1.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    0.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8918    0.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6579   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437   -0.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -0.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  1  0  0  0
 12  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14  9  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 18 24  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
M  END


  Mrv2104 03262307212D          

 25 29  0  0  1  0            999 V2000
    2.1427    1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899    0.9995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6649    0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915   -0.6748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1620   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0742   -0.2747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844   -0.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5089    0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0325    1.3390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765   -0.8434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1245    0.7311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9578    1.5391    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.5866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8995    1.3416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1621    0.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5465    0.7557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0076    1.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    0.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8918    0.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6579   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437   -0.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -0.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  1  0  0  0
 12  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14  9  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 18 24  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC(=O)[C@@]3(O)[C@]1([H])[C@H](C)C=C[C@]2(O)[C@@]31OC2=C(O1)C=C(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-8-3-4-10-11(7-8)23-17(22-10)15(19)6-5-9(2)12-13(15)21-14(18)16(12,17)20/h3-7,9,12-13,19-20H,1-2H3/t9-,12+,13-,15-,16+,17+/m1/s1

> <INCHI_KEY>
DRZJXCJMRJFUEG-NCPWRRBTSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.309

> <EXACT_MASS>
316.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.19458560871776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2S,2'R,3'R,6'R,8'R)-6',8'-dihydroxy-3',5-dimethyl-10'-oxaspiro[1,3-benzodioxole-2,7'-tricyclo[4.4.0.0^{2,8}]decan]-4'-en-9'-one

> <JCHEM_LOGP>
1.8277179423333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.638025189354245

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.226195434566325

> <JCHEM_PKA_STRONGEST_BASIC>
-4.326712771265329

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
77.60550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,2'R,3'R,6'R,8'R)-6',8'-dihydroxy-3',5-dimethyl-10'-oxaspiro[1,3-benzodioxole-2,7'-tricyclo[4.4.0.0^{2,8}]decan]-4'-en-9'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-23         0                                  
HETATM    1  C   UNK     0       4.000   3.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.715   1.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.974   0.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.645  -0.691   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.344  -1.260   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.169  -2.255   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.005  -0.513   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.531  -0.300   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.950   1.242   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.061   2.500   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0       0.890  -1.574   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       2.099   1.365   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       1.788   2.873   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       2.925   1.095   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.546   2.504   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.036   0.048   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.753   1.411   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.271   1.149   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.481   2.102   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.911   1.531   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.131   0.007   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.561  -0.565   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.922  -0.946   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.491  -0.375   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.110  -1.056   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   16                                             
CONECT    6    5                                                            
CONECT    7    5    8   11   12                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    7    2   13   14                                             
CONECT   13   12                                                            
CONECT   14   12    9   15   16                                             
CONECT   15   14                                                            
CONECT   16   14    5   17   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   18   23   25                                                  
CONECT   25   24   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₆

Average Mass

316.3090 Da

Monoisotopic Mass

316.09469 Da

IUPAC Name

(1'R,2S,2'R,3'R,6'R,8'R)-6',8'-dihydroxy-3',5-dimethyl-10'-oxaspiro[1,3-benzodioxole-2,7'-tricyclo[4.4.0.0^{2,8}]decan]-4'-en-9'-one

Traditional Name

(1'R,2S,2'R,3'R,6'R,8'R)-6',8'-dihydroxy-3',5-dimethyl-10'-oxaspiro[1,3-benzodioxole-2,7'-tricyclo[4.4.0.0^{2,8}]decan]-4'-en-9'-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC(=O)[C@@]3(O)[C@]1([H])[C@H](C)C=C[C@]2(O)[C@@]31OC2=C(O1)C=C(C)C=C2

InChI Identifier

InChI=1S/C17H16O6/c1-8-3-4-10-11(7-8)23-17(22-10)15(19)6-5-9(2)12-13(15)21-14(18)16(12,17)20/h3-7,9,12-13,19-20H,1-2H3/t9-,12+,13-,15-,16+,17+/m1/s1

InChI Key

DRZJXCJMRJFUEG-NCPWRRBTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	u3224002@iwate-u.ac.jp	The United Graduate School of Agricultural Sciences, Iwate University	ryuhi kanehara	2024-07-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	u3224002@iwate-u.ac.jp	The United Graduate School of Agricultural Sciences, Iwate University	ryuhi kanehara	2024-07-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	u3224002@iwate-u.ac.jp	The United Graduate School of Agricultural Sciences, Iwate University	ryuhi kanehara	2024-07-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	u3224002@iwate-u.ac.jp	The United Graduate School of Agricultural Sciences, Iwate University	ryuhi kanehara	2024-07-12	View Spectrum
HMQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	u3224002@iwate-u.ac.jp	The United Graduate School of Agricultural Sciences, Iwate University	ryuhi kanehara	2024-07-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	u3224002@iwate-u.ac.jp	The United Graduate School of Agricultural Sciences, Iwate University	ryuhi kanehara	2024-07-12	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Gluconolactones

Alternative Parents

Substituents

Gluconolactone
Benzodioxole
Ketal
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Benzenoid
Oxane
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Meta-dioxole
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.83	ChemAxon
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.61 m³·mol⁻¹	ChemAxon
Polarizability	31.19 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for paraphaeolactone C2 (NP0333604)

MOL for NP0333604 (paraphaeolactone C2)

3D MOL for NP0333604 (paraphaeolactone C2)

3D SDF for NP0333604 (paraphaeolactone C2)

3D-SDF for NP0333604 (paraphaeolactone C2)

PDB for NP0333604 (paraphaeolactone C2)

3D PDB for NP0333604 (paraphaeolactone C2)

SMILES for NP0333604 (paraphaeolactone C2)

INCHI for NP0333604 (paraphaeolactone C2)

Structure for NP0333604 (paraphaeolactone C2)

3D Structure for NP0333604 (paraphaeolactone C2)